1,2,3,4-tetrahydrospiro-β-carboline-(3S)-carboxamide-1,2'-(1,3')-indanedione | 927210-38-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1,2,3,4-tetrahydrospiro-β-carboline-(3S)-carboxamide-1,2'-(1,3')-indanedione
• 英文别名: (3S)-1',3'-dioxospiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,2'-indene]-3-carboxamide
• CAS: 927210-38-6
• 化学式: C₂₀H₁₅N₃O₃
• 分子量: 345.357
• InChiKey: ZCKHGTNPAGYJLH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydrospiro-β-carboline-(3S)-carboxamide-1,2'-(1,3')-indanedione 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以46%的产率得到14-hydroxy-(3,14,15,16,17,18,19,20)-octadehydro-21-yohimbanone-(5S)-carboxamide
  参考文献：
  名称：

  Ninhydrin as a building block for yohimbanones, β-carbolines, and oxyprotoberberines

  摘要：

  Condensation of ninhydrin with tryptamide or tryptamine followed by Lewis acid-induced rearrangement provided yohimbanones that were readily converted to beta-carbolines via oxidative ring cleavage. The analogous condensation-rearrangement with 3,4-dimethoxyphenethylamine and ninhydrin afforded an oxyprotoberberine, which was further oxygenated at the 13a position. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.115
• 作为产物：
  描述：

  水合茚三酮 、 L-色氨酰胺盐酸盐 以 盐酸 为溶剂， 反应 24.0h， 以73%的产率得到1,2,3,4-tetrahydrospiro-β-carboline-(3S)-carboxamide-1,2'-(1,3')-indanedione
  参考文献：
  名称：

  Ninhydrin as a building block for yohimbanones, β-carbolines, and oxyprotoberberines

  摘要：

  Condensation of ninhydrin with tryptamide or tryptamine followed by Lewis acid-induced rearrangement provided yohimbanones that were readily converted to beta-carbolines via oxidative ring cleavage. The analogous condensation-rearrangement with 3,4-dimethoxyphenethylamine and ninhydrin afforded an oxyprotoberberine, which was further oxygenated at the 13a position. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.115

文献信息

• Ninhydrin as a building block for yohimbanones, β-carbolines, and oxyprotoberberines
  作者：Laura L. Tomasevich、Nicole M. Kennedy、Stephen M. Zitelli、R. Troy Hull、Chelsey R. Gillen、Suet K. Lam、Neal J. Baker、John C. Rohanna、Jason M. Conley、Marcy L. Guerra、Mari Lynne Starr、Justine B. Sever、Patrick J. Carroll、Michael S. Leonard

  DOI：10.1016/j.tetlet.2006.11.115

  日期：2007.1

  Condensation of ninhydrin with tryptamide or tryptamine followed by Lewis acid-induced rearrangement provided yohimbanones that were readily converted to beta-carbolines via oxidative ring cleavage. The analogous condensation-rearrangement with 3,4-dimethoxyphenethylamine and ninhydrin afforded an oxyprotoberberine, which was further oxygenated at the 13a position. (c) 2006 Elsevier Ltd. All rights reserved.